Sinteza novih derivata 2-arilbenzimidazola Pd-kataliziranim reakcijama unakrsnog spajanja i njihova strukturna karakterizacija

master's thesis

• Title (english): Synthesis of novel 2-arylbenzimidazole derivatives by using Pd-catalyzed cross-coupling reactions and their structural characterization
• Author: Antonija Jelčić
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Dajana Kučić Grgić (član povjerenstva)
• Committee member: Ida Boček Pavlinac (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2023-09-27, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U ovom radu opisana je sinteza novih derivata 2-arilbenzimidazola Pd-kataliziranim reakcijama unakrsnog spajanja i njihova strukturna karakterizacija 1H- i 13C-NMR spektroskopijom. Reakcijom 4-hidroksibenzaldehida s natrijevim metabisulfitom kao oksidansom pripravljena je natrijeva sol hidroksi(4-hidroskifenil)metansulfonske kiseline (1) koja je mikrovalovima potpomognutom reakcijom kondenzacije s o-diaminobenzenom prevedena u 2-(4-hidroksifenil)benzimidazol (2). Reakcijom kondenzacije natrijeve soli hidroksi(4-hidroskifenil)metansulfonske kiseline (1) s 5-klor-o-fenildiaminom pripravljen je 2-(4-hidroskifenil)5-klorbenzimidazol (5). Reakcijom alkiliranja 4-hidroksibenzaldehida s odgovarajućim alkil-halogenidima pripravljeni su O-alkilirani derivati benzaldehida (10–20), od kojih su samo oni s morfolinskim supstituentom reakcijom kondenzacije s
5-klor-ofenildiaminom uspješno prevedeni u 5-klorbenzimidazolne derivate (21–29).
Suzuki-Miyaurinom reakcijom unakrsnog spajanja derivata benzimidazola 21, 23 i 26) s fenilboronskom kiselinom uz Pd-katalizator pripravljeni su 5-fenilbenzimidazolni derivati (30–32).

Abstract (english)

This work describes the synthesis of new 2-arylbenzimidazole derivatives by Pd-catalyzed cross-coupling reactions and their structural characterization by 1H- and 13C-NMR spectroscopy. The sodium salt of hydroxy(4-hydroxyphenyl)methanesulfonic acid (1) was prepared by the reaction of 4-hydroxybenzaldehyde with sodium metabisulfite as an oxidant, which was converted into 2-(4-hydroxyphenyl)benzimidazole (2) by a microwave-assisted condensation reaction with o-diaminobenzene. The condensation reaction of the sodium salt of hydroxy(4-hydroskyphenyl)methanesulfonic acid (1) with 5-chloro-o-phenyldiamine prepared 2-(4-hydroskyphenyl)5-chlorobenzimidazole (5). O-alkylated benzaldehyde derivatives (10–20) were prepared by the alkylation reaction of 4-hydroxybenzaldehyde with corresponding alkyl halides, of which only those with a morpholine substituent were successfully converted into 5-chlorobenzimidazole derivatives (21–29) by condensation reaction with 5-chloro-o-phenyldiamine. 5-phenylbenzimidazole derivatives (30–32) were prepared by the Suzuki-Miyaura cross-coupling reaction of benzimidazole derivatives (21, 23 and 26) with phenylboronic acid and a Pd-catalyst.

• Keywords: benzimidazol; reakcije unakrsnog spajanja; Suzuki-Miyaurina reakcija
• Keywords (english): benzimidazole; cross-coupling reactions; Suzuki-Miyaura reaction
• Language: croatian
• URN:NBN: urn:nbn:hr:149:022528
• Project: Number: IP-2018-01-4682; Title: Novi spojevi temeljeni na bioizosterima purina za ispitivanje njihovih antitumorskih i antipatogenih djelovanja; Acronym: PurBioCaPa; Leader: Silvana Raić-Malić; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: IP
• Study programme: Title: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Environmental chemistry and green technologies; Study programme type: university; Study level: graduate; Academic / professional title: sveučilišni/a magistar/magistra primijenjene kemije (sveučilišni/a magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Embargoed access; Embargo expiration date: 2025-10-01
• Created on: 2023-11-23 13:48:17